Diethyl Ether → (4-(5-Fluoro-2-methoxypyridin-4-yl)-3-(1-vinylcyclopentyl)phenyl)methanol

HRID 404391Notes

Reaction equation

[F:1][C:2]1[C:3]([C:10]2[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][C:11]=2[C:20]2([CH:25]=[CH2:26])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)C>C1COCC1>[F:1][C:2]1[C:3]([C:10]2[CH:19]=[CH:18][C:13]([CH2:14][OH:15])=[CH:12][C:11]=2[C:20]2([CH:25]=[CH2:26])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(1-vinylcyclopentyl)benzoate 26.5 (51.0 mg, 143 μmol) in THF (2.0 mL) was slowly added LAH, (1.0 M solution in diethyl ether (0.30 mL, 287 μmol)) at room temperature. The resulting mixture was stirred at 50° C. for 1 hour. The product was obtained after work up and solvent removal. The desired product was used in the next step without further purification. MS ESI (pos.) m/e: 328.2 (M+H)+.

Workup

customat room temperature
customThe product was obtained after work up
customsolvent removal
customThe desired product was used in the next step without further purification

Sources & evidence

ORD record: ord-a0e83c3fd8ea414a82f8e274cc8403f7
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748462B2

Reaction notes

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